The catalytic asymmetric total synthesis of elatol

Journal of the American Chemical Society

Volumn 130, Issue 3, 2008, Pages 810-811

  White, David E ^a   Stewart, Ian C ^a   Grubbs, Robert H ^a   Stoltz, Brian M ^a  

^a California Institute of Technology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA CHAMIGRENE; APLYDACTONE; BETA CHAMIGRENE; CHAMIGRENE; ELATOL; JOHNSTONOL; LAURENCENONE B; LAURENCENONE C; LIGAND; MAJUSCULONE; NATURAL PRODUCT; OBTUSOL; PALLADIUM; SESQUITERPENE; UNCLASSIFIED DRUG; VINYL CHLORIDE;

ALKYLATION; ARTICLE; ASYMMETRIC SYNTHESIS; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; ENANTIOSELECTIVITY; RING CLOSING METATHESIS; STEREOCHEMISTRY; SYNTHESIS;

CATALYSIS; SESQUITERPENES; SPIRO COMPOUNDS; STEREOISOMERISM;

EID: 38349159026     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja710294k     Document Type: Article

References (37)

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26. 2 led to significantly less conversion.
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31. 1H NMR .
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34. 11C NMR data for semisynthetic (+)-laurencenone B ((+)-7) (ref 17b) matched that of our synthetic material. See the supporting information for a detailed comparison.
35. Purification of α-bromoketone 10 was hampered by its poor stability to silica gel and reverse phase HPLC.
36. Determined by quenching the reaction at -78°C in a separate run, resulting in the isolation a 3.9:1 mixture of alcohol diastereomers favoring i. (Chemical Equation Presented)
37. D value for the synthetic material would be +95.5°, which differed from the observed value by 3.6%.